A Superior Synthesis of Longitudinally Twisted Acenes
| Autor: | Kathleen V. Kilway, Gene-Hsiang Lee, Bharat Kumar, Dustin D. Patterson, Elizabeth M. Menuey, Robert G. Clevenger |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Anthracene 010405 organic chemistry Stereochemistry Organic Chemistry Diol General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Hexacene Catalysis 0104 chemical sciences Quinone Pentacene chemistry.chemical_compound Tetracene Hydrocarbon chemistry Acene |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 24(1) |
| ISSN: | 1521-3765 |
| Popis: | Seven longitudinally twisted acenes (an anthracene, two tetracenes, three pentacenes, and a hexacene) have been synthesized by the addition of aryllithium reagents to the appropriate quinone precursors, followed by SnCl2 -mediated reduction of their diol intermediates, and several of these acenes have been crystallographically characterized. The new syntheses of the three previously reported twisted acenes, decaphenylanthracene (1), 9,10,11,20,21,22-hexaphenyltetrabenzo[a,c,l,n]pentacene (2), and 9,10,11,12,13,14,15,16-octaphenyldibenzo[a,c]tetracene (14), resulted in a reduction of the number of synthetic steps. As a consequence their overall yields were increased by factors of 50-, 24-, and 66-fold, respectively. All of the twisted acene syntheses reported here are suitable for the synthesis of at least gram quantities of these remarkable hydrocarbon materials. |
| Databáze: | OpenAIRE |
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